Hydrochloric Acid → 2-Amino-4-cyano-3-hydroxynitrobenzene

HRID 2378433Notes

Reaction equation

HRID 2378433 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12])#[N:2].[I-].C[N+:15](C)(C)N.[O-]OOO[O-].[Na+].[Na+].Cl>CS(C)=O>[NH2:15][C:5]1[C:4]([OH:12])=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 2861482-Hydroxy-4-nitrobenzonitrileHCID 131725183CID 131725183

Product 1

HCID 218754622-Amino-4-cyano-3-hydroxynitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Compound 477A (0.438 g, 2.67 mmol) was dissolved in 25 mL of DMSO and trimethylhydrazinium iodide (0.534 g, 2.67 mmol) was added. Sodium pentoxide (0.880 g, 8.01 mmol) was added under N2 to give a deep red solution and stirring was continued overnight at rt. The reaction mixture was poured into 50 mL of 10% HCl and extracted with EtOAc (2×25 mL). The combined organic layers were washed with water (25 mL), brine (25 mL), dried over sodium sulfate and concentrated in vacuo to give compound 477B as an oily red solid which was used directly in the next reaction without further purification.

Workup

  1. customto give a deep red solution
  2. extractionextracted with EtOAc (2×25 mL)
  3. washThe combined organic layers were washed with water (25 mL), brine (25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8acec3164ff4f29a45d72ab21600a64
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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